Cake shortening containing acetylated monoglycerides and method of making same



United States Patent CAKE SHORTENING CONTAINING ACETYLATED MONOGLYCERIDES AND METHOD OF MAK- ING SAME No Drawing. Application February 27, 1957 Serial No. 642,659

3 Claims. (Cl. 99-118) This invention relates to shortenings, and more particularly to an improved Shortening for cake and the like.

Cake shortenings are commonly produced from triglycerides to which various amounts and kinds of emulsifying agents may be added. The triglycerides may be partially or fully hydrogenated, rearranged and/or interesterified. These triglycerides may then be used as they are or they may be blended in various proportions. The prior art is replete with information on procuring and preparing composite shortenings of various melting points and having various degrees of plasticity. Emulsifiers such as lecithin, monoglycerides, mixtures of monoand diglycerides and other surface active agents have been added to triglycerides to improve the emulsifying properties and to change the plasticity of the shortening. It is generally accepted that monoglycerides are more potent as emulsifiers than diglycerides.

It is also well known that basestock of shortening can be appropriately modified modified with respect to its plasticity by substituting acetyl groups for fatty acid groups in the molecular structure thereof. Thus, Patent Number 2,614,937 discloses a number of examples wherein hydrogenated oils were treated with triacetin and the resulting products rearranged to bring about the desired plasticity and melting point. p

The instant invention is concerned with improving the emulsification properties of the shortening for specific purposes while preserving proper plasticity. It is, therefore, a general object of the invention to provide a shortening which will produce a superior cake having an improved texture, grain, flavor, volume, and eating quality.

More specifically, it is an object of the invention to provide a shortening which has been admixed with incompletely acetylated monoglycerides to achieve combinative improvements in its plasticity and emulsifying properties.

In attempting to determine the elfect of various acetylated produces on the shortening characteristics of fatty acid triglycerides, it was noted that certain experimentation resulted in somewhat improved cakes when the shortenings therefrom were incorporated into such cake and then baked. Further experimental work was, therefore, indicated to establish whether acetylated products are beneficial in cake formulae and, if so, how the acetylation should be conducted, to what extent it should be carried out, and at what concentration the product should be blended into a triglyceride shortening base for best results. v

Three general procedural routes were followed to determine how the acetylation should be carried out:

1. INTERESTERIFICATION OF FATTY ACID TRI- GLYCERIDES WITH TRIACETIN Basestocks variously of animal and vegetable fats, essentially triglycerides, were blended with triacetin in different proportions and reacted, using a conventional catalyst, sodium methylate, for rearrangment. A mixture of the following triglycerides resulted:

(a) Triacetin (triglyceride with three acetyl groups); (b) Triglycerides with two acetyl groups;

(c) Triglycerides with one acetyl group;

(d) Triglycerides without acetyl groups.

The composition of the mixture obtained varies with the proportions of triglyceride basestock and triacetin mixed at the start and is the random or probability distribution for that particular starting mixture.

It was found that the fat and triacetin must be thorougly dry at the start to prevent destruction of the catalyst and the catalyst itself must be freshly prepared or kept in bottles sealed shut with wax. after each portion is withdrawn. Otherwise, an incomplete reaction may be obtained due to previous destruction by atmospheric moisture of much of the catalyst.

The above experiment was carried out using mol.

of triacetin to 1 mol. of basestock. Rearranged lard, tallow, hydrogenated soybean oil and a blend of hydrogenated soybean and cottonseed oil were all tried as basestock. The experiments were repeated, using first Ms mol. of triacetin and then 1. mol. to 1 mol. of basestock.

In each case, the volatiles (mostly unreacted triacetin) were stripped off in a steam deodorizer and the resulting fat plasticized and incorporated into standard white cake mix of the following formulation:

White cake formula The resultant cakes were not promising. All were inferior to a control cake made with the same formula above and using a standard commercial shortening.

A further attempt to match the performance of the control cake was made by blending the above interesterified products with their respective parent basestocks to a saponification value of 200.6, which was the saponification value of the control. Bake tests on these shortenings, however, were unsatisfactory and this route was consequently abandoned.

'2. INTERESTERIFICATION OF MONOGLYCER- IDES WITH TRIACETIN A commercial peanut monoglyceride stock (about 40% alpha-monoglycerides) was blended with triacetin in various proportions and reacted using sodium methylate as catalyst. A more complex mixture of the following ten glycerides resulted:

a. Triglycerides i. Triglycerides with no acetyl groups;

Triglycerides with one acetyl group;

iii. Triglycerides with two acetyl groups;

iv. Triglycerides with three acetyl groups (triacetin). b. Diglyceridesi. Diglycerides with no acetyl groups;

ii. Diglycerides with one acetyl group;

iii. Diglycerides with two acetyl groups (di-acetin). c. Monoglycerides-- i. Monoglycerides without acetyl group;

Monoglycerides with one acetyl group (monoacetin).

d. Glycerine.

Again, the composition of the resultant mixture varied with the proportions of monoglyceride stock and triacetin used at the start, a random distribution of the above ten possible components being obtained in each case. Two products were made, starting with (l) 0.7 mol. peanut monoglycerides and 0.3 mol. triacetin, and (2) 0.5 mol. monoglycerides and 0.5 mol. triacetin.

Each of the above (1) and (2) was blended in five difierent proportions with rearranged lard, and also in the same proportions with a mixture of hydrogenated cottonseed and soya oils known in the trade as Vream to produce the following twenty shortenings:

(1) Rearranged lard (75% +product (1) above (25 (2) Rearranged lard (80% +product 1) above (20%) (3) Rearranged lard 85 +product 1) above (15%) (4) Rearranged lard (90% +product (1) above (10%) (5) Rearranged lard (95 +product (1) above (5%) (6 Rearranged lard (75%)+product (2) above (25%) (7) Rearranged lard (80%)+product (2) above (20%) (8) Rearranged lard (85% +product (2) above (15%) (9) Rearranged lard (90%)+product (2) above (10%) 10) Rearranged lard (95% +product (2) above (5%) (11) Vream (regular) (75% +product (1) above (25% (12) Vream (regular) (80%)+product (1) above (20%) (13) Vream (regular) (85%)+product (1) above (14) Vream (regular) (90%)+product (1) above (10%) (15) Vream (regular) (95% +product (1) above (5% (16) Vream (regular) (75% +product (2) above (25%) (17) Vream (regular) (80%)+product (2) above (18) Vream (regular) (85 +product (2) above (15 (19) Vream (regular) (90% +product (2) above (10%) (20) Vream (regular) (95% +product (2) above (5%) All twenty shortenings were plasticized and incorporated into cake mixes. The performance of the 0.7 mol. product and the 0.5 mol. product were nearly the same, and the best cakes were obtained when 20% of the product was incorporated into 80% of the Vream basestock. Although none of the cakes was quite equal to the control cake in volume, grain and texture, the performance was better than when shortenings prepared by interesterifying triglycerides with triacetin were used.

Independent bake tests using triacetin in the shortening components were found to give unsatisfactory results, and no emulsification action was observed in baked cakes, using the above standard formula. It was also found that, from the standpoint of baking performance, cakes made from shortening into which was incorporated mono glycerides with one acetyl group and diglycerides with two acetyl groups showed no improvement over those made with the plain basestock in the absence of an emulsifier. In the light of the foregoing independent bake tests and of the unsatisfactory bake tests made with shortening blended with triglycerides having one or two acetyl groups, it is an important generalization of this invention that glyceride additive to conventional basestock shortenings enhance the baking properties of cakes when the glyceride is a diglyceride of the type which contains one acetyl group, one long-chained fatty acid group and one hydroxyl group, such diglyceride being hereafter arbitrarily called 6-3. This is opposite to the generally accepted viewpoint that diglycerides are less potent as emulsifiers than monoglycerides.

Since peanut oil, which was interesterified with triacetin in the foregoing procedure Number 2, originally contains only about 40% alpha-monoglycerides, a more concentrated source was sought for purposes of better determining the effective ranges of different proportions of our diglyceride emulsifier component in basestock shortenings. Molecularly distilled monostearin having over alpha-monoglycerides and known commercially as Myverol 18-06 a product of Distillation Products, Inc.) was obtained for this purpose.

The above monostearin (Myverol 18-06) was then interesterified with triacetin at the rate of 0.6 mol. monostearin and 0.4 mol. of triacetin. The volatiles were stripped off and bake tests performed on shortening made from 25%, 20%, 15%, 10% and 5% of the product, respectively, in (a) rearranged lard and (b) Vream (the same as that used above), The baking results on the cakes containing the product at the 20% and 15% level were best, the 15% level appearing to give the better resuits of two. These levels in Vream were particularly excellent and appeared to be equal or superior to the control cake in volume, texture, grain and all other respects.

3. ACETYLATION OF MONOGLYCERIDES WITH ACETIC ANHYDRIDE The commercial peanut monoglyceride stock used above was acetylated to intermediate levels of (1) 25% and (2) 35% with acetic anhydride, since preliminary work had already indicated favorable results on a product acetylated to the 12.4% level and less favorable results on the 48.4% level acetylated product. A mixture of the following glycerides were obtained:

a. Triglyceridesi. Triglycerides with no acetyl groups, ii. Triglycerides with one acetyl group, iii. Triglycerides with two acetyl groups. b. Diglyceridesi. Diglycerides with no acetyl groups; ii. Diglycerides with one acetyl group. 0. Monoglyceridesi. Monoglycerides with no acetyl groups.

The above products (1) and (2) were made by adjusting the ratio of acetic anhydride to peanut monoglycerides so that 25% and 35% acetylation occurred, respectively. After stripping off volatiles, the products were plasticized into various basestocks at the levels of 25%, 20%, 15%, 10% and 5%.

Bake tests were made on the above ten shortenings. The 35 acetylated product yielded fair cakes with the best at the 20% level. The 20% and 25% acetylated product gave two cakes as good as, or better than, the control cake. The 15% level gave a very good cake, but not quite as good as the first two.

To prepare a product with the maximum concentration of our diglyceride component, G-3, monostearin (molecularly distilled) was acetylated with acetic anhya. Monoglycerides b. Diglycerides with one acetyl group (G-3) c. Triglycerides with two acetyl groups Acetylations were carried out using enough acetic anhydride to eifect slightly less than 50% acetylation in an attempt to (a) maximize the formation of a diglyccride with one acetyl group and (b) minimize the formation of a triglyceride with two acetyl groups. The net result was the production of more of the desired diglyceride, G-3, and less di-acetyl monostearin.

A series of acetylations were first carried out varying the time from two and one-half hours to five hours, and then to seven and one-half hours, all at atmospheric pressure, allowing the reaction mixture to reflux at 140 degrees centigrade. A second series of acetylations was carried out under pressure, allowing the pressure to increase to ten pounds above atmospheric pressure, and holding it there by maintaining the required temperature.

Results of bake tests on the above acetylated products and on interesterified products made from monostearin and also from commercial peanut monoglycerides, by rearranging with triacetin are given in the following tables at the different levels of emulsifier indicated. Although the cake volume is of great importance in the overall quality of the cake, other factors, such as grain, texture, fragility, ease of pan removal and eating quality are of significance. Despite the subjective nature of the latter qualities, it is necessary to represent them numerically to arrive at a number which represents the composite cake quality. Hence, in the column headed Cake quality, the figures given represent the sequence from best to poorest and were obtained by a careful inspection of the cake in question.

Other factors, such as specific gravity of the batter, are of use as a guide, but are not infallible. Although all good cakes resulted from batters of low gravity, not all the batters of low gravity produced good cakes.

Various triglyceride bases were used with the prepared emulsifiers and in the percentages of base indicated in the following tables, parallel results being evident for all the base employed. The specific tables presented herein relate to a basestock shortening made from a mixture of hydrogenated cottonseed and soya oils but are characteristic of the behavior of all such basestocks as rearranged lard, peanut oil and marine oils when intermixed with the specific emulsions and in the proportions noted.

TABLE I.CAKES MADE FROM SHOR'IENING CONTAIN- ING EMULSIFIER PLUS 95% BASESTOCK (1.) ,ACETYLATED MONOSTEARIN AND ACETYLATED COMMERCIAL MONOGLYCERIDES Cake Quality Rating Description of Percent G-3 Cake Description of in total Product Vol. Cake Average grain and (l) Glycerol Monotexture.

steaaatg 2% hrs.

Acetylated 90% Glycerol Monostearate 7% hrs. 1 atm. Acetylated 90% Glycerol Monostearate 23 hrs. 1 atm. Acetylated Peanut Oil Mono- .glycerides 37.7%

Acetylation. -Acetylated Peanut Oil Monoglycerides 23.7% Acetylatlon. Completely Acetylated Product (Aldocet). Acetylated Mono giyceride (Myvacet).

17 11.. -1- Acety1ated'90% Compact, thick cell walls.

Compact grain (3) and thick cell walls.

Worst of series Compact, fiat cake; worst.

951 Compact, flat (7) poor cake.

Worst in series- (2) INTERESTERIFIED PRODUCTS 34.5 Mole Ratio: (0.6 1, 090 Fine grain but 1 6 1n.) Myverol, slightly heavy 154 in.) Trlacecell walls. 24.1 Mole Ratlo: (0.7 995 Slight compact 2 E.) Pelanutgil thick cell wallzls;

onog yceri e ve oorca e. 10 93 In.) Trace- W p in. 27.6 Mole Ratio: (0.5 967 Compact, poor (3) m.) Peanut Oil cake. Monoglyceride, (0.5 m.) Triacetin.

TABLE II.CAKES MADE FROM SHORTENING CONTAIN- ING 10% EMULSIFIER PLUS 90% BASESTOCK (1) AOETYLATED MONOSTEARIN AND ACETYLATED COMMERCIAL MONOGLYCERIDES Percent G-3 Description of Cake Description of Cake in total Product Vol. Cake Quality emulsifier Rating 76.7 Acetylated 90% 1, 125 Fine, even grain, (2)

Glycerol Monothin cell walls, stearate 2 hrs. good shape; l0#-S. best cake. 0.0 Completely Accty- 974 Bready texture (9) lated Prodand grain, very not (Aldocet). poor.

77.7 Acetylated 90% 1, 160 Fine, even grain (1) Glycerol Monoand texture, stearate 2% hrs. thin cell walls; 10#-S. best cakes 10 and 15%. 58.3 Acetylated 90% 1, 133 Fine, even grain (3) Glycerol Monoand texture, stcarate 7% hrs. thin cell walls;

@ 1 atm. best cakes 10% and 15%. 44.5 Acetylated Mono- 1, 038 Not as good as (7) glyceride 15% level; grain (Myvacct). more compact. 57.3 Acetylated 90% l, 232 Fragile cake but (4) Glycerol Monogood texture 4 stearate 2% hrs. and grain.

1 atm. 32.8 Acetylated Pea- 1, 056 Cake only fair, (6)

nut oil Monograin and texglyceridcs 37.7% ture all right but Acetylation. not superior. 21.6 Acetylated Pea- 1, 059 Cake not good; (8) nut Oil Monomore openglycerides 23.7% grained. Acetylation. 28.6 Acetylated Men- 1, 072 Cake finer (5) haden Oil grained than Monoglycerides. Peanut Oil Minoglycerlde ca e.

(2) INTERESTERIFIED PRODUCTS 34.5 Mole Ratio: 1,152 Fair grain and 1) (0.6 m texture, slightly Myverol, heavy cell (0.4 Ill.) Triwalls, next to acetin. worst. 24.7 Mole Ratio: 965 Only fair cake, (3)

(0.7 m.) Peanut slightly heavy Oil Monoglyccell walls.

erldes, (0.3 m.) Triacetin. 27.6 Mole Ratio: 1,090 Not good texture (2) (0.5 m.) Peanut and grain, def- Oil Monoglycinltely interior. erldes, (0.5 in.) Triacetin.

TABLE III.CAKES MADE FROM SHORTENING CONTAIN- ING 15% EMULSFIEB PLUS 85% BASES/TOOK 1 AOETYLATED MONOSTEARIN AND AOETYLATED COMMERCIAL MONOGLYOERIDES Percent G-B Description of Cake Description of Cake in total Product Vol. Cake Quality emulsifier Rating 76.7 Acetylated 90% 1, 140 Almost as good as (2) Glycerol Mono- 10% level cake stearate 2 hrs. which was rated 7 1o#-s. +100. 77.7 Acetylated 90% 1, 180 Fine, even- (1) Glycerol Monograined cake, stearate 2% hrs. almost as fine 10#-S. as 10%. 58.3 Acetylated 90% 1, 133 Not quite, but

Glycerol Monoalmost as good stearate 7% hrs. as at 1 atm. 57.3 Acetylated 90% 1, 264 Best of series but (3) Glycerol Monomuch too fragstearate 2% hrs. ile. 1 atm. 27.6 Acetylated Pea- 1, 102 (Jake fair in grain (8) nut Oil Monoand Texture glycerides 21.5% but not super- Acetylation. ior. 21.6 Acetylated Pea- 1,1 84 Not as good as (7) nut Oil Mono: level glycerides 23.7% cakes. Acetylation. 0.0 Completely Acet- 989 Bready grain and (9) ylated Product xture. (Aldocet). 28.6 Acetylated Men- 1, 102 Better than Pea- (6) haden Oil nut Oil Mono- Monoglyceride glyceride cake 22.6% Acetylaof same level.

1011. 44.6 Acetylated Mono- 1, 129 Best of Myvacet (4) glyceride series-good (Myvacet). grain and texture.

(2) INTERESTERIFIED PRODUCTS 34.5 Mole Ratio: (0.6 1, 256 Texture and (1) m.) Myverol, grain good. 150.4 m.) Triacein. 24.7 Mole Ratio: (0.7 1,033 Not particularly (3) m.) Peanut Oil good-sharply Monoglyceride, below the 20% t(0.3 m.) Triacecake.

in. 27.6 Mole Ratio: (0.5 1, 044 Texture and (2) m.) Peanut Oil Grain fair-not Monoglyceride, outstanding. (0.5 m.) Triacetin.

TABLE IV.-OAKES MADE FROM SHO RTENING COMP RIS- ING 20% EMULSIFIER PLUS 80% BASESTOCK COMMERCIAL MONOGLYCE RIDES Percent G-3 Description of Cake Description of Cake in total Product Vol. Cake Quality emulsifier Rating 58.9 Acetylated 90% 1, 140 Good cake but (6) Glycerol Monooptimum was stearate 7% hrs. at 10%-15% 1 atm. level.

57.3 Acetylated 90% 1, 145 Average grain (7) Glycerol Monoand texture but stearate 2 hrs. fragile.

l atrn.

27.6 Acetylated Pea- 1, 110 Grain and texture (3) nut Oil Mononot quite equal glycerides 21.5% to control cake Acetylation. but close.

32.8 Acetylated Pea- 1, 132 Best of series but (4) nut Oil Mononot as good as glycerides 37.7% above cake.

Acetylation.

21.6 Acetylated Pea- 1, 240 Good cake-2nd (2) nut Oil Monobest of series. glycerides 23.7%

Acetylation.

28.6 Acetylated Men- 1, 178 Best of Acety- (1 haden Oil lated series; Monoglycerides better than 22.6% Acety- Aoetylated Pealation. nut Oil Monoglyceride 20%+75.

0.0 Completely 966 Bready, coarse (8) Acetylated grain and tex- Product ture. (Aldocet).

44.5 Acetylated Mono- 1,122 2nd Best cake of (5) glyceride Myvacet series (Myvacet) (15% level best).

(2) INTERESTERIFIED PBODUGTB Mole Ratio: (0.6 m.) Myverol, (0.4 m.) Triacetin.

Mole Ratio: (0.7

m.) Peanut Oil Monoglycerldes, (0.3 m.) Triacetin.

Mole Ratio: (0.5

In.) Peanut Oil Monoglycerides, (0.5 m.) Triacetin.

Fairly good texture and grain- 2nd best in series.

Best of seriesgood texture and grain.

Good texture and grain.

TABLE V.CAKES MADE FROM SHORTENING CONTAIN- ING 25% EMULSIFIER PLUS 75% BASESTQCK (1) AOETYLAIED MONOSTEARIN AND ACETYLATED COMMERCIAL MONOGLYOERIDES Percent G-B Description of Cake Description of Cake in total Product Vol. Cake Quality emulsifier Rating 58.3 Acetylated 1,140 Fairly good but (7) Glycerol Mononot quite as stearate 7% hrs. good as 20% 1 atm. level.

57.3. Acetylated 90% 1,160 Average in tax (8) Glycerol Monoture and grain stearate 2 5 hrs. but very fragile 1 atm. cake.

27.6 Acetylated Pea- 1,133 Not quiteequal to (3) nut Oil Monocontrol cake on glyceride 21.5% grain and tex- Acetylation. ture, but close.

32.8 Acetylated Pea- 1,079 2nd best cake of (5) nut Oil Monoseries; good texglycerides 37.7% ture and grain. Acetylation.

21.6 Acetylated Pea- 1,256 Good cake-aver- (1) nut Oil Monoage grain and glycerides 23.7% texture.

Acetylation.

38.8 Acetylated Pen- 1,150 Good cake-not (4) nut Oil Monoquite up to glycerides 48.4% control cake.

Acetylation.

28.6 Acetylated Men- 1,185 2nd best of Acet- (2) haden Oil ylation series; Monoglyceride better than 22.6% Acetyla- 2Pfieanut Oil 44.5 Acetylated Mono- 1, 099 25% not as good (6) glyceride as 20%, 15%,

(Myvacet) but almost as good.

(2) INTERESTERIFIED PRODUCTS 34.5 Mole Ratio: (0.6 1, 224 Not so good tex- (1) m.) Myverol, ture and grain- (0.4 m.) 3rd best in acetin. series.

24.7 Mole Ratio: (0.7 1, 094 2nd best in series; (3)

m.) Peanut Oil average texture Monoglycerides, and grain.

(0.3 In.) Triacetin.

27.6 Mole Ratio: (0.6 1,160 Fair texture and (2) m.) Peanut Oil graln-rnot Monoglycerides, outstanding.

.5 m.) Triacetin.

By way of comparison, an average production control cake utilizing the foregoing white cake formula outlined above with an ordinary commercial shortening and a conventional emulsifier rated 1110 when judged by the same standards as the cakes outlined in the tables.

Referring to Table I above, when the base stock short-.- ening constituted of the total shortening and the specific emulsifiers constituted but 5% of the total shortening, none of the cakes baked therefrom were, on a par with the production control cake, although it appeared significant that, as the percentage of G-3 in the emulsifier increased, the cake quality rose in value and appeared best at the 77% level of G4 in the emulsifier component.

Referring to Table II, where the total shortening corn sisted of 90% base stock shortening and 10% of the emulsifier component, the cakes baked at the lows! Cir-3 concentrations in the emulsifier were still not good, but

quality increased rapidly as the percentage of G 3 increased. Cakes better than the production control cake were obtained when the emulsifier component at the level contained between 58% and 77% of G-3.

Referring to Table III, when the total shortening contained 85% basestock and of the various specific emulsifiers, improvement was noted even at the low G-3 percentages in the emulsifier and the cakes were generally equal or better than the production control cake rated at 1110. As in the case of the cakes rated in Table II, the higher concentration of G3 in the emulsifier produced very good cakes and the quality consistently increased with an increase in the G-3 content.

Referring to Table IV, the total shortening consisted of 80% basestock shortening and of the specific emulsifier. Very good cakes were produced even at lower G-3 concentration in the emulsifier, but at 58% G-3 in the emulsifier component the cake quality again dropped off and approached production control quality. It, therefore, appeared that an optimum condition existed which was related to the G-3 concentration in the emulsifier and that higher concentrations would result in a reversal in cake quality.

As a check on the behavior of cakes at the optimum concentration of G-3 in the emulsifier, a still higher level of specific emulsifier was employed as set forth in Table V where 75% basestock shortening was employed in combination with of the specific emulsifier. Here, again, it was evident that excellent cakes were produced at the lower levels of 6-3 content in the emulsifier and that, as the G-3 content increased, an optimum was again reached beyond which cake quality gradually diminished.

The data from the above tables indicates that, as the G-3 content of the shortening component of the cake mix increases, the cake quality rises until an optimum is reached, after which the cake quality decreases somewhat with further increase of G-3 content. It is evident that the optimum amount of 6-3 in the total mix can be attained by using a greater percentage of the emulsifier component in the shortening having a lower G-3 content, or by using a lesser quantity of emulsifier in the shortening, but having a higher G-3 content. It appears consistent throughout all of the experimental work above noted that G3 content is largely responsible for the behavior of the cake quality. Minor variations in cake quality ratings with respect to 6-3 content are within the range of error of baking procedure and product analysis. Beyond the optimum G-3 content over-emulsification accounts for the decline in cake quality. It is, of course, known that deleterious effects can be obtained in any cake mix where the product is over-emulsified. Thus,

reason would dictate that in producing an optimum cake, one would not deliberately add an excess of 6-3 or any other conventional emulsifier-s which may tend towards over-emulsifiying the mix.

Relating the foregoing data to the G-3 content, it becomes apparent that a range of from 3% to 15% of G-3 in the total shortening will give consistent improve ment to conventional basestock shortenings when used in a conventional cake mix. The 6-3 product is a diglyceride which contains one acetyl group, one longchained fatty acid group, and one hydroxyl group, hence is pin-pointed as an extraordinary cake improver when incorporated as an emulsifier in conventional basestock shortening. The percentage of the G-3 component does not materially alter or interfere with the selected consistency of the basestock shortening and, hence, permits a wide range of combinative formulation requiring but little experimentation to achieve the improved results noted.

What we claim is:

1. A shortening product comprising from to 97% of an edible triglyceride oil and 3% to 15% of a diglyceride having one long-chain fatty acid group, one acetyl group and one hydroxyl group.

2. The method of producing a cake shortening; said method consisting in reacting an edible glyceride oil, said glyceride oil comprising mixtures of triglycerides and monoglycerides, with triacetin in the presence of an esterification catalyst to produce a reaction product having between 3% and 15 of a diglyceride having one longchain fatty acid group, one acetyl group and one hydroxyl group.

3. The method of producing a cake shortening; said method consisting in reacting an edible glyceride oil, said glyceride oil comprising mixtures of triglycerides and monoglycerides, with acetic anhydride to produce a reaction product having between 3% and 15% of a diglyceride having one long-chain fatty acid group, one acetyl group and one hydroxyl group.

References Cited in the file of this patent UNITED STATES PATENTS 2,132,701 Richardson et a1. Oct. 11, 1938 2,745,749 Feuge et a1. May 15, 1956 2,764,605 Embree et al. Sept. 25, 1956 OTHER REFERENCES Feuge: Acetoglycerides-New Fat Products of P0- tential Value to the Food Industry, Food Technology, June 1955, pp. 314-318. 

1. A SHORTENING PRODUCT COMPRISING FROM 85% TO 97% OF AN EDIBLE TRIGLYCERIDE OIL AND 3% TO 15% OF A DIGLYCERIDE HAVING ONE LONG-CHAIN FATTY ACID GROUP, ONE ACETYL GROUP AND ONE HYDROXYL GROUP. 